A Facile Strategy for Non-fluorinated Intrinsic Low-<italic style="font-style: italic">k</italic> and Low-loss Dielectric Polymers: Valid Exploitation of Secondary Relaxation Behaviors

Chao Qian; Zhen-Guo Fan; Wei-Wen Zheng; Run-Xin Bei; Tian-Wen Zhu; Si-Wei Liu; Zhen-Guo Chi; Matthew P. Aldred; Xu-Dong Chen; Yi Zhang; Jia-Rui Xu

doi:10.1007/s10118-020-2339-4

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A Facile Strategy for Non-fluorinated Intrinsic Low-k and Low-loss Dielectric Polymers: Valid Exploitation of Secondary Relaxation Behaviors

ARTICLE | Updated：2019-10-22

- A Facile Strategy for Non-fluorinated Intrinsic Low-k and Low-loss Dielectric Polymers: Valid Exploitation of Secondary Relaxation Behaviors
- A Facile Strategy for Non-fluorinated Intrinsic Low-k and Low-loss Dielectric Polymers: Valid Exploitation of Secondary Relaxation Behaviors
- Chinese Journal of Polymer Science 2020年38卷第3期页码：213-219
- Affiliations：
  
  PCFM Lab, GD HPPC Lab, Guangdong Engineering Technology Research Centre for High-performance Organic and Polymer Photoelectric Functional Films, State Key Laboratory of Optoelectronic Materials and Technologies, School of Chemistry, Sun Yat-sen University, Guangzhou 510275, China
- Author bio：
  
  ceszy@mail.sysu.edu.cn
- Funds：
  
  This work was finincially supported by the National Natural Science Foundation of China (Nos. 51373204 and 51873239), the National 973 Program of China (No. 2014CB643605), the Science and Technology Project of Guangdong Province (Nos. 2015B090915003 and 2015B090913003), the Leading Scientific, Technical and Innovation Talents of Guangdong Special Support Program (No. 2016TX03C295), the China Postdoctoral Science Foundation (No. 2017M612801), and the Fundamental Research Funds of Sun Yat-sen University.
- DOI：10.1007/s10118-020-2339-4
  中图分类号：
- 收稿：2019-06-14，
  
  修回：2019-7-27，
  
  录用：2019-8-7，
  
  网络首发：2019-10-22，
  
  纸质出版：2020-03
- Accepted：
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Qian, C.; Fan, Z. G.; Zheng, W. W.; Bei, R. X.; Zhu, T. W.; Liu, S. W.; Chi, Z. G.; Aldred, M. P.; Chen, X. D.; Zhang, Y.; Xu, J. R. A facile strategy for non-fluorinated intrinsic low-k and low-loss dielectric polymers: valid exploitation of secondary relaxation behaviors. Chinese J. Polym. Sci. 2020, 38, 213–219.

Chao Qian, Zhen-Guo Fan, Wei-Wen Zheng, et al. A Facile Strategy for Non-fluorinated Intrinsic Low-k and Low-loss Dielectric Polymers: Valid Exploitation of Secondary Relaxation Behaviors[J]. Chinese Journal of Polymer Science, 2020, 38(3): 213-219. DOI: 10.1007/s10118-020-2339-4.
Qian, C.; Fan, Z. G.; Zheng, W. W.; Bei, R. X.; Zhu, T. W.; Liu, S. W.; Chi, Z. G.; Aldred, M. P.; Chen, X. D.; Zhang, Y.; Xu, J. R. A facile strategy for non-fluorinated intrinsic low-k and low-loss dielectric polymers: valid exploitation of secondary relaxation behaviors. Chinese J. Polym. Sci. 2020, 38, 213–219. DOI： 10.1007/s10118-020-2339-4.

Chao Qian, Zhen-Guo Fan, Wei-Wen Zheng, et al. A Facile Strategy for Non-fluorinated Intrinsic Low-k and Low-loss Dielectric Polymers: Valid Exploitation of Secondary Relaxation Behaviors[J]. Chinese Journal of Polymer Science, 2020, 38(3): 213-219. DOI: 10.1007/s10118-020-2339-4. DOI：

摘要

Abstract

High-performance low-

and low-loss circuit materials are urgently needed in the field of microelectronics due to the upcoming Fifth-Generation Mobile Communications Technology (5G Technology). Herein

a facile design strategy for non-fluorinated intrinsic low-

and low-loss polyimides is reported by fully considering the secondary relaxation behaviors of the polymer chains. A new amorphous non-fluorinated polymer (TmBPPA) with a

value of 2.23 and a loss tangent lower than 3.94 × 10

−3

at 10

Hz has been designed and synthesized

which to the best of our knowledge is the lowest value amongst the non-fluorinated and non-porous polymers reported in literature. Meanwhile

TmBPPA exhibits excellent overall properties

such as excellent thermostability

good mechanical properties

low moisture absorption

and high bonding strength. As high-performance flexible circuit materials

all these characteristics are highly expected to meet the present and future demands for high density

high speed

and high frequency electronic circuit used in 5G wireless networks.

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references

Volksen, W.; Miller, R. D.; Dubois, G . Low dielectric constant materials . Chem. Rev. , 2010 . 110 56 - 110 . DOI: 10.1021/cr9002819 http://doi.org/10.1021/cr9002819 .

Maier, G . Low dielectric constant polymers for microeletronics . Prog. Polym. Sci. , 2001 . 26 3 - 65 . DOI: 10.1016/S0079-6700(00)00043-5 http://doi.org/10.1016/S0079-6700(00)00043-5 .

Miller, R. D . In search of low- k dielectrics . Science , 1999 . 286 421 - 423 . DOI: 10.1126/science.286.5439.421 http://doi.org/10.1126/science.286.5439.421 .

Hecht, J . The bandwidth bottleneck that is throttling the internet . Nature News , 2016 . 536 139 - 142 . DOI: 10.1038/536139a http://doi.org/10.1038/536139a .

Andrews, J. G.; Stefano, B.; Wan, C.; Stephen, V. H.; Angel, L.; Anthony, C. K. S.; Zhang, J. C . What will 5G be? . IEEE Journal on Selected Areas in Communications , 2014 . 32 1065 - 1082 . DOI: 10.1109/JSAC.2014.2328098 http://doi.org/10.1109/JSAC.2014.2328098 .

Shamiryan, D.; Abell, T.; Iacopi, F.; Maex, K . Low- k dielectric materials . Mater. Today , 2004 . 7 34 - 39 . .

Morgen, E. M.; Ryan, T.; Zhao, J. Hua.; Hu, C.; Cho, T.; Ho, P. S . Low dielectric constant materials for ULSI interconnects . Annu. Rev. Mater. Sci. , 2000 . 30 645 - 680 . DOI: 10.1146/annurev.matsci.30.1.645 http://doi.org/10.1146/annurev.matsci.30.1.645 .

Kohl, P. A . Low-dielectric constant insulators for future integrated circuits and packages . Annu. Rev. Chem. Biomol. Eng. , 2011 . 2 379 - 401 . DOI: 10.1146/annurev-chembioeng-061010-114137 http://doi.org/10.1146/annurev-chembioeng-061010-114137 .

Zhang, G. X.; Tkatchenko, A.; Paier, J.; Appel, H.; Scheffler, M . Van der Waals interactions in ionic and semiconductor solids . Phy. Rev. Lett. , 2011 . 107 245501 DOI: 10.1103/PhysRevLett.107.245501 http://doi.org/10.1103/PhysRevLett.107.245501 .

Krause, B.; Diekmann, K.; van der Vegt, N. F. A.; Wessling, M . Open nanoporous morphologies from polymeric blends by carbon dioxide foaming . Macromolecules , 2002 . 35 1738 - 1745 . DOI: 10.1021/ma011672s http://doi.org/10.1021/ma011672s .

Krause, B.; Koops, G. H.; van der Vegt, N. F. A.; Wessling, M.; Wubbenhorst, M.; van Turnhout, J . Ultralow- k dielectrics made by supercritical foaming of thin polymer films . Adv. Mater. , 2002 . 14 1041 - 1046 . DOI: 10.1002/1521-4095(20020805)14:15<1041::AID-ADMA1041>3.0.CO;2-A http://doi.org/10.1002/1521-4095(20020805)14:15<1041::AID-ADMA1041>3.0.CO;2-A .

Long, T. M.; Swager, T. M . Molecular design of free volume as a route to low- k dielectric materials . J. Am. Chem. Soc. , 2003 . 125 14113 - 14119 . DOI: 10.1021/ja0360945 http://doi.org/10.1021/ja0360945 .

Eslava, S.; Urrutia, J.; Busawon, A. N.; Baklanov, M. R.; Lacopi, F.; Aldea, S.; Maex, K.; Martens, J. A.; Kirschhock, C. E. A . Zeolite-inspired low- k dielectrics overcoming limitations of zeolite films . J. Am. Chem. Soc. , 2008 . 130 17528 - 17536 . DOI: 10.1021/ja8066572 http://doi.org/10.1021/ja8066572 .

Ro, H. W.; Char, K.; Jeon, E.; Kim, H. J.; Kwon, D.; Lee, H. J.; Lee, J. K.; Rhee, H. W.; Soles, C.; Yoon, D. Y . High-modulus spin-on organosilicate glasses for nanoporous applications . Adv. Mater. , 2007 . 19 705 - 710 . DOI: 10.1002/adma.200601528 http://doi.org/10.1002/adma.200601528 .

Connor, E. F.; Sundberg, L. K.; Kim, H. C.; Cornelissen, J. J.; Magbitang, T.; Rice, P. M.; Lee, V. Y.; Hawker, C. J.; Volksen, W.; Hedrick, J. L.; Miller, R. D . Templating of silsesquioxane cross-linking using unimolecular self-organizing polymers . Angew. Chem. Int. Ed. , 2003 . 115 3915 - 3918 . DOI: 10.1002/ange.200350930 http://doi.org/10.1002/ange.200350930 .

Lee, Y. K.; Murarka, S. P.; Jeng, S. P.; Auman, B . Investigations of the low dielectric constant fluorinated polyimide for use as the interlayer dielectric in ULSI . Materials Research Society Symposium Proceedings , 1995 . 381 31 - 43 . DOI: 10.1557/PROC-381-31 http://doi.org/10.1557/PROC-381-31 .

Lee, Y. K.; Murarka, S. P.; Auman, B . Thermal curing conditions for low k -fluorinated polyimide film for use as the interlayer dielectric in ULSI . Materials Research Society Symposium Proceedings , 1996 . 443 71 - 77 . DOI: 10.1557/PROC-443-71 http://doi.org/10.1557/PROC-443-71 .

Dubois, G.; Volksen, W.; Magbitang, T.; Miller, R. D.; Gage, D. M.; Dauskardt, R. H . Molecular network reinforcement of sol-gel glasses . Adv. Mater. , 2007 . 19 3989 - 3994 . DOI: 10.1002/adma.200701193 http://doi.org/10.1002/adma.200701193 .

Mary, A. B. M.; Wright, S.; Sandberg, A.; Nguyen, B. N.; Van Keuls, F. W.; Mueller, C. H.; Rodríguez-Solís, R.; Miranda, F. A . Low dielectric polyimide aerogels as substrates for lightweight patch antennas . ACS Appl. Mater. Interfaces , 2012 . 4 6346 - 6353 . DOI: 10.1021/am301985s http://doi.org/10.1021/am301985s .

Liu, Y.; Zhang, Y.; Lan, Q.; Liu, S.; Qin, Z.; Chen, L.; Zhao, C.; Chi, Z.; Xu, J.; Economy, J . High-performance functional polyimides containing rigid nonplanar conjugated triphenylethylene moieties . Chem. Mater. , 2012 . 24 1212 - 1222 . DOI: 10.1021/cm3003172 http://doi.org/10.1021/cm3003172 .

Liu, Y.; Qian, C.; Qu, L.; Wu, Y.; Zhang, Y.; Wu, X.; Zou, B.; Chen, W.; Chen, Z.; Chi, Z.; Liu, S.; Chen, X.; Xu, J . A bulk dielectric polymer film with intrinsic ultralow dielectric constant and outstanding comprehensive properties . Chem. Mater. , 2015 . 27 6543 - 6549 . DOI: 10.1021/acs.chemmater.5b01798 http://doi.org/10.1021/acs.chemmater.5b01798 .

Taki, K.; Hosokawa, K.; Takagi, S.; Mabuchi, H.; Ohshima M . Rapid production of ultralow dielectric constant porous polyimide films via CO 2 - tert -amine zwitterion-induced phase separation and subsequent photopolymerization . Macromolecules , 2013 . 46 2275 - 2281 . DOI: 10.1021/ma302406m http://doi.org/10.1021/ma302406m .

Chen, Y.; Wang, W.; Yu, W.; Yuan, Z.; Kang, E. T.; Neoh, K. G.; Krauter, B.; Greiner, A. . Nanoporous low- k polyimide films via poly(amic acid)s with grafted poly(ethylene glycol) side chains from a reversible addition-fragmentation chain-transfer-mediated process . Adv. Funct. Mater. , 2004 . 14 471 - 478 . DOI: 10.1002/adfm.200305050 http://doi.org/10.1002/adfm.200305050 .

Kawagishi, K.; Saito, H.; Furukawa, H.; Horie, K. . Superior nanoporous polyimides via supercritical CO 2 drying of jungle-gym-type polyimide gels . Macromol. Rapid Commun. , 2007 . 28 96 - 100 . DOI: 10.1002/marc.200600587 http://doi.org/10.1002/marc.200600587 .

Zhang, Y. H.; Lu, S. G.; Li, Y. Q.; Dang, Z. M.; Xin, J. H.; Fu, S. Y.; Li, G. T.; Guo, R. R.; Li, L. F . Novel silica tube/polyimide composite films with variable low dielectric constant . Adv. Mater. , 2005 . 17 1056 - 1059 . DOI: 10.1002/adma.200401330 http://doi.org/10.1002/adma.200401330 .

Liao, W. H.; Yang, S. Y.; Hsiao, S. T.; Wang, Y. S.; Li, S. M.; Ma, C. C. M.; Tien, H. W.; Zeng, S. J . Effect of octa(aminophenyl) polyhedral oligomeric silsesquioxane functionalized graphene oxide on the mechanical and dielectric properties of polyimide composites . ACS Appl. Mater. Interfaces , 2014 . 6 15802 - 15812 . DOI: 10.1021/am504342j http://doi.org/10.1021/am504342j .

Lew, C. M.; Li, Z. J.; Shuang, L.; Hwang, S. J.; Liu, Y.; Medina, I. D.; Sun, M. W.; Wang, J. L.; Davis, M. E.; Yan, Y. S . Pure-silica-zeolite MFI and MEL low-dielectric-constant films with fluoro-organic functionalization . Adv. Funct. Mater. , 2008 . 18 3454 - 3460 . DOI: 10.1002/adfm.200800390 http://doi.org/10.1002/adfm.200800390 .

Yuan, C.; Jin, K.; Li, K.; Diao, S.; Tong, J.; Fang, Q . Non-porous low- k dielectric films based on a new structural amorphous fluoropolymer . Adv. Mater. , 2013 . 25 4875 - 4878 . DOI: 10.1002/adma.201302021 http://doi.org/10.1002/adma.201302021 .

Yang, J.; Liu, S.; Zhu, F.; Huang, Y.; Li, B.; Zhang, L . New polymers derived from 4-vinylsilylbenzocyclobutene monomer with good thermal stability, excellent film-forming property, and low-dielectric constant . J. Polym. Sci., Part A: Polym. Chem. , 2011 . 49 381 - 391 . DOI: 10.1002/pola.24437 http://doi.org/10.1002/pola.24437 .

Zhao, X. Y.; Liu, H. J . Review of polymer materials with low dielectric constant . Polym. Int. , 2010 . 59 597 - 606 . .

Chern, Y. T.; Shiue, H. C . Low dielectric constants of soluble polyimides based on adamantane . Macromolecules , 1997 . 30 4646 - 4651 . DOI: 10.1021/ma970520n http://doi.org/10.1021/ma970520n .

Wang, J.; Zhou, J.; Jin, K.; Wang, L.; Sun, J.; Fang Q . A new fluorinated polysiloxane with good optical properties and low dielectric constant at high frequency based on easily available tetraethoxysilane (TEOS) . Macromolecules , 2017 . 50 9394 - 9402 . DOI: 10.1021/acs.macromol.7b02000 http://doi.org/10.1021/acs.macromol.7b02000 .

Zhang, K.; Han, L.; Froimowicz, P.; Ishida, H . A smart latent catalyst containing o -trifluoroacetamide functional benzoxazine: Precursor for low temperature formation of very high performance polybenzoxazole with low dielectric constant and high thermal stability . Macromolecules , 2017 . 50 6552 - 6560 . DOI: 10.1021/acs.macromol.7b00887 http://doi.org/10.1021/acs.macromol.7b00887 .

Chern, Y. T.; Shiue, H. C . High subglass transition temperatures and low dielectric constants of polyimides derived from 4,9-bis(4-aminophenyl) diamantine . Chem. Mater. , 1998 . 10 210 - 216 . DOI: 10.1021/cm970341k http://doi.org/10.1021/cm970341k .

Johari, G. P.; Goldstein, M . Viscous liquids and the glass transition. II. Secondary relaxations in glasses of rigid molecules . J. Chem. Phys. , 1970 . 53 2372 - 2388 . DOI: 10.1063/1.1674335 http://doi.org/10.1063/1.1674335 .

Jho, J. Y.; Yee, A. F . Secondary relaxation motion in bisphenol a polycarbonate . Macromolecules , 1991 . 24 1905 - 1913 . DOI: 10.1021/ma00008a031 http://doi.org/10.1021/ma00008a031 .

Wimberger-Friedl, R.; Schoo, H. F. M . On the secondary relaxation of substituted bis-A polycarbonates . Macromolecules , 1996 . 29 8871 - 8874 . DOI: 10.1021/ma960028o http://doi.org/10.1021/ma960028o .

Ngai, K. L.; Beiner, M . Secondary relaxation of the Johari-Goldstein kind in alkyl nanodomains . Macromolecules , 2004 . 3721 8123 - 8127 . .

Coburn, J. C.; Soper, P. D.; Auman, B. C . Relaxation behavior of polyimides based on 2,2′-disubstituted benzidines . Macromolecules , 1995 . 28 3253 - 3260 . DOI: 10.1021/ma00113a030 http://doi.org/10.1021/ma00113a030 .

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2026-9 Contents

A Facile Strategy for Non-fluorinated Intrinsic Low-k and Low-loss Dielectric Polymers: Valid Exploitation of Secondary Relaxation Behaviors

A Facile Strategy for Non-fluorinated Intrinsic Low-k and Low-loss Dielectric Polymers: Valid Exploitation of Secondary Relaxation Behaviors

DOI：10.1007/s10118-020-2339-4

摘要

Abstract

关键词

Keywords

references